Tri/penta/aza-tetracyclo-dodeca/enes/dienes or-decaenes

ABSTRACT

New and valuable polycyclic compounds which contain nitrogen-containing rings and have a strong action on plants, agents for influencing plant growth containing these compounds, and a method of influencing plant growth with these compounds.

This is a division of application Ser. No. 781,767, filed Mar. 28, 1977,now U.S. Pat. No. 4,189,434.

The present invention relates to new and valuable polycyclic compounds,processes for their manufacture, crop protection agents containing thesecompounds, and their use as crop protection agents.

We have found that compounds of the formula ##STR1## where A denotes theradical --N═N--, B denotes the radicals ##STR2## denotes the radicals##STR3## n denotes one of the integers 0 and 1, m denotes one of theintegers 0 and 1, and R¹ denotes hydrogen, alkyl of 1 to 30 carbonatoms, alkenyl of 2 to 30 carbon atoms, alkynyl of 2 to 30 carbon atoms(preferably alkyl of 1 to 18 carbon atoms)--all of which may be linearor branched, cyclic or acyclic--, phenyl, naphthyl, or a more highlycondensed aromatic radical, a heterocyclic radical with one or morehetero atoms (O, N, S), or aralkyl, it being possible for the aromaticradical to be substituted by a heterocycle, the abovementioned radicals,apart from hydrogen, being unsubstituted or mono- or polysubstituted byhalogen (F, Cl, Br, I) or pseudo-halogen ##STR4## primary, secondary ortertiary alkyl, haloalkyl, haloalkoxy, haloalkylmercapto, or the radical##STR5## Alk denoting alkyl and Ar denoting an aromatic radical, and R¹may additionally denote, when m is O, (Alk, Ar)₃ Si--, (Alk, Ar)₃ SN--and, when m is 1, --OAlk(Ar), --SAlk(Ar), the radical ##STR6## and R²and R³ are identical or different and each denotes (B)_(m) --R⁴, R⁴having the same meanings as R¹, and salts of these compounds, have astrong biological action on plants.

It is known to prepare compounds III-V, where R═CH₃ -- and C₂ H₅ --, bythe following route: reaction of quadricyclane with azodicarboxylic acidesters (II) to give III, which is converted to IV by saponification anddecarboxylation and oxidized, without isolation of IV, by CuCl₂ to theCu^(I) complex of the azo compound V (JACS, 91, 5668, 1969). ##STR7##

Compound VI is obtained by partial saponification and decarboxylation ofIII.

The active ingredients according to the invention may be prepared asfollows:

1. Preparation of the compounds described in Examples 1 and 2 and thetables relating thereto. Reaction of compounds III-VI with alkyl, aryl,aralkyl, sulfonyl, silyl, stannyl or heterocyclic azides or diazidessynthesized by known methods (Houben-Weyl, 10/3, 777).

The reaction takes place in an indifferent solvent, e.g., petroleumether, benzene, xylene, methylene chloride, chloroform, chlorobenzene,ether, tetrahydrofuran, dioxane, dimethylformamide and mixture ofsolvents, such as dioxane/water, the solvent depending on the solubilityof the azide employed, at from -20° to +180° C., preferably +20° to 120°C. The reaction products precipitate out from the reaction solutioneither on cooling or, if polar solvents are used, upon addition ofnonpolar solvents, or may be obtained by concentrating the solution.

During the reaction, Δ² -1,2,3-triazoline derivatives are formed, someof which, e.g., sulfonyl azides or azides in which the azide group is inconjugation with strongly electronegative substituents, already convertunder the reaction conditions to exo- and/or endo-aziridine derivativesby elimination of nitrogen.

The addition of silyl azides to the C═C double bond gives N-silyl-Δ²-1,2,3-triazoline derivatives from which the corresponding N--H-Δ²-1,2,3-triazoline derivatives are formed upon treatment withethanol/ligroin.

2. Preparation of the compounds described in Examples 3 and 4 and thetables relating thereto. Elimination of nitrogen from the Δ²-1,2,3-triazoline compounds to give the corresponding aziridinederivatives.

The elimination takes place in the abovementioned solvents either uponheating at from 90° to 140° C. or, after addition of acid catalysts, atfrom 20° to 80° C. Examples of suitable catalysts are acids (e.g.,sulfuric acid, acetic acid, trifluoroacetic acid) and insoluble carriersubstances containing acidic groups (e.g., ion exchangers).

3. Preparation of the compounds described in Example 5 and the tablerelating thereto. Reaction of N--H-- ² -1,2,3-triazoline orN--H-aziridine derivatives with carboxylic or thiocarboxylic acidhalides, carboxylic acid anhydrides, chlorocarbonates,thiochlorocarbonates, phosgene, sulfonyl halides, sulfenyl halides,alkyl halides, alkenyl halides, alkynyl halides, aralkyl halides,aldehydes, ketones, isocyanates, mustard oils, and carbamoyl andthiocarbamoyl halides, the corresponding N-substituted triazoline andaziridine derivatives being formed either by elimination of hydrogenhalide or by addition of the N--H group to the C═O or C═N double bond.

The reactions are carried out in known manner in inert solvents andusually in the presence of bases, e.g., tertiary amines, alkali metalcarbonates or bicarbonates, sodium methylate, alkali metal hydroxides,etc., at from 20° to 100° C.

4. The reaction of compounds IV and VI with the substances listed under(3) gives the corresponding N-substituted and N,N'-disubstitutedderivatives (Example 6), which are then reacted as described above under(1) and (2) (Example 2, 4).

5. The reaction of quadricyclane with alkyl, aryl or aralkylazodicarboxylic acid diesters gives the corresponding N,N'-disubstitutedderivatives (Example 6), which are then reacted as described above under(1) and (2) (Example 2, 4).

Generally, the compounds may be prepared by any of the processes givenunder (1), (2) and (3) above. However, the process for which theindividual examples and tables are given is usually the mostadvantageous of the various methods possible.

The structure of the active ingredients was confirmed by nmr, infraredand mass spectroscopy or ultimate analysis.

The melting points given are uncorrected.

EXAMPLE 1 ##STR8##

72 parts (by weight) of compound V and 92 parts of p-chlorophenylazideare heated in 240 parts of benzene for 5 hours at 80° C. After themixture has cooled to room temperature, the Δ² -1,2,3-triazolinederivative which has formed is suction filtered and washed with 50 partsof petroleum ether; yield: 148 parts (90% of theory); m.p.: 192°-193° C.(decomposes). ##STR9##

12 parts of V and 25 parts of 2-hydroxy-3-azido-5-chlorobenzenesulfonicacid are heated in 500 parts of dioxane/water (4:1) for 8 hours at 80°C. After the solvent has been distilled off in vacuo at 25 mbars, theresidue is washed (digested) with 500 parts of benzene; yield: 32 parts(93% of theory); m.p.: 135° C. (decomposes). ##STR10##

3 parts of V and 8.1 parts of perfluorobutylsulfonylazide are stirred in15 parts of benzene for 20 hours at room temperature. After the benzenehas been distilled off at 50 mbars, the residue is digested with 50parts of petroleum ether; yield: 9 parts (86% of theory); m.p.: 115° C.(decomposes).

The following compounds were prepared analogously:

    ______________________________________                                         ##STR11##                                                                                                    m.p.                                          R.sup.1             n     m     [°C.]                                  ______________________________________                                        H                   1     0     136 (decomposes)                              CH.sub. 3           0     1     135 (decomposes)                              C.sub.3 H.sub.7     1     0      56 (decomposes)                              C.sub.8 H.sub.17    0     1      96 (decomposes)                              C.sub.12 H.sub.25   1     0      63 (decomposes)                               ##STR12##          1     0     100                                           CH.sub.2COOCH.sub.3 1     0      76                                           CH.sub.2CN          1     0      94 (decomposes)                               ##STR13##          1     0      76                                           CH.sub.2CH.sub.2N(C.sub.3 H.sub.7).sub.2                                                          1     0      54                                           (CH.sub.2).sub.3N(C.sub.2 H.sub.5).sub.2                                                          1     0      16                                            ##STR14##          1     0      62                                           CH.sub.2C.sub.6 H.sub.5                                                                           1     0     100                                            ##STR15##          1     0      88 (decomposes)                               ##STR16##          1     0     164 (decomposes)                               ##STR17##          1     0     170 (decomposes)                               ##STR18##          1     0     159 (decomposes)                               ##STR19##          1     0     191 (decomposes)                               ##STR20##          1     0     124 (decomposes)                               ##STR21##          1     0     144 (decomposes)                              C.sub.6 H.sub.5     1     0     149 (decomposes)                              C.sub.6 H.sub.5     0     1     119 (decomposes)                               ##STR22##          1     0     159 (decomposes)                               ##STR23##          0     1     135 (decomposes)                              p-BrC.sub.6 H.sub.4 1     0     185 (decomposes)                              p-ClC.sub.6 H.sub.4 0     1     125 (decomposes)                              p-NO.sub.2C.sub.6 H.sub.4                                                                         1     0     192 (decomposes)                              p-CH.sub.3 OC.sub.6 H.sub.4                                                                       1     0     153 (decomposes)                              p-CH.sub.3C.sub.6 H.sub.4                                                                         1     0     159 (decomposes)                              p-CH.sub.3C.sub.6 H.sub.4                                                                         0     1     126 (decomposes)                               ##STR24##          1     0     187 (decomposes)                              p-FC.sub.6 H.sub.4  1     0     156 (decomposes)                              p-C.sub.3 H.sub.7C.sub.6 H.sub.4                                                                  1     0     168 (decomposes)                              p-HOOCC.sub.6 H.sub.4                                                                             1     0     182 (decomposes)                               ##STR25##          1     0     216 (decomposes)                              p(C.sub.2 H.sub.5).sub.2 NC.sub. 6 H.sub.4                                                        1     0     123 (decomposes)                              o-ClC.sub.6 H.sub.4 1     0     120 (decomposes)                              o-BrC.sub.6 H.sub.4 1     0     102 (decomposes)                              o-CH.sub.3C.sub.6 H.sub.4                                                                         1     0     105 (decomposes)                              o-NO.sub.2C.sub.6 H.sub.4                                                                         1     0     168 (decomposes)                              o-NO.sub.2C.sub.6 H.sub.4                                                                         0     1     185 (decomposes)                              m-ClC.sub.6 H.sub.4 1     0     152 (decomposes)                              m-BrC.sub.6 H.sub.4 1     0     172 (decomposes)                              m-NO.sub.2C.sub.6 H.sub.4                                                                         1     0     193 (decomposes)                              m-CH.sub.3C.sub.6 H.sub.4                                                                         1     0     151 (decomposes)                              m-CF.sub.3C.sub.6 H.sub.4                                                                         1     0     145 (decomposes)                              m-C.sub.3 H.sub.7C.sub.6 H.sub.4                                                                  1     0     127 (decomposes)                               ##STR26##          1     0     182 (decomposes)                               ##STR27##          1     0     143 (decomposes)                               ##STR28##          1     0     113 (decomposes)                               ##STR29##          1     0     162 (decomposes)                               ##STR30##          1     0     173 (decomposes)                               ##STR31##          1     0     141 (decomposes)                               ##STR32##          1     0     127 (decomposes)                               ##STR33##          1     0     152 (decomposes)                               ##STR34##          1     0      78 (decomposes)                               ##STR35##          1     0     186 (decomposes)                               ##STR36##          1     0     175 (decomposes)                               ##STR37##          1     0     129 (decomposes)                               ##STR38##          1     0     159 (decomposes)                               ##STR39##          1     0     168 (decomposes)                               ##STR40##          1     0     166 (decomposes)                               ##STR41##          1     0     168 (decomposes)                               ##STR42##          1     0     164 (decomposes)                               ##STR43##          1     0     191 (decomposes)                               ##STR44##          1     0     164 (decomposes)                               ##STR45##          1     0     131 (decomposes)                               ##STR46##          1     0     189 (decomposes)                               ##STR47##          0     0     187 (decomposes)                               ##STR48##          0     0     255 (decomposes)                               ##STR49##          0     0     150 (decomposes)                               ##STR50##          1     0     181 (decomposes)                               ##STR51##          1     0     136 (decomposes)                               ##STR52##          1     0     196 (decomposes)                               ##STR53##          1     0     184 (decomposes)                               ##STR54##          0     0     250 (decomposes)                               ##STR55##          1     0     136 (decomposes)                               ##STR56##          1     0     132 (decomposes)                               ##STR57##          1     0     184 (decomposes)                               ##STR58##          0     0     155 (decomposes)                               ##STR59##          1     0      60 (decomposes)                               ##STR60##          1     0     188 (decomposes)                               ##STR61##          0     0     150 (decomposes)                               ##STR62##          1     0     199 (decomposes)                               ##STR63##          0     0     211 (decomposes)                               ##STR64##          1     0     220 (decomposes)                               ##STR65##          1     0     147 (decomposes)                               ##STR66##          1     0     175 (decomposes)                               ##STR67##          1     0     183 (decomposes)                               ##STR68##          1     0     183 (decomposes)                               ##STR69##          0     0     218 (decomposes)                               ##STR70##          0     0      92 (decomposes)                               ##STR71##          1     0     214 (decomposes)                               ##STR72##          1     0      69 (decomposes)                               ##STR73##          1     0     138 (decomposes)                               ##STR74##          1     0     112 (decomposes)                               ##STR75##          1     0     160                                           ______________________________________                                    

EXAMPLE 2 ##STR76##

24 parts of III and 20 parts of p-bromophenylazide are heated in 80parts of benzene for 5 hours at 80° C. After the mixture has cooled toroom temperature, the reaction product is suction filtered and washedwith 50 parts of petroleum ether; yield: 38 parts (86% of theory); m.p.:217°-218° C. (decomposes). ##STR77##

12 parts of III and 9 parts of phenylsulfonylazide are heated in 100parts of chlorobenzene for 6 hours at 100° C. After the solvent has beendistilled off at 25 mbars, the residue is digested with 100 parts ofpetroleum ether; yield: 18 parts (97% of theory); m.p.: 146° C.(ethanol/ligroin).

Compounds in which R² and/or R³ denote H may also be present in the formof their salts, for instance as salts with mineral acids, e.g., ashydrochlorides.

The following compounds were prepared analogously:

    __________________________________________________________________________     ##STR78##                                                                                                                     m.p.                         R.sup.1     R.sup.2        R.sup.3           n m °C.                   __________________________________________________________________________    H           COOCH.sub.3    COOCH.sub.3       1 0  83 (decomposes)             H.sub.3     "              "                 0 1 100 (decomposes)             C.sub.3 H.sub.7                                                                           "              "                 1 0  86 (decomposes)             CH.sub.2COOCH.sub.3                                                                       "              "                 1 0 169 (decomposes)             CH.sub.2C.sub.6 H.sub.5                                                                   "              "                 1 0 118 (decomposes)             C.sub.6 H.sub.5                                                                           "              "                 1 0 157 (decomposes)             "           COOC.sub.2 H.sub.5                                                                           COOC.sub.2 H.sub.5                                                                              1 0 125 (decomposes)              ##STR79##  H              H                 1 0 135 (decomposes)              ##STR80##  "              "                 1 0 129 (decomposes)              ##STR81##  .sup.++ H      COOCH.sub.3       1 0 138 (decomposes)              ##STR82##  .sup.++ H      COOCH.sub.3       1 0  85 (decomposes)              ##STR83##  COOCH.sub.3    COOCH.sub.3       1 0 212 (decomposes)             "           .sup.++COOCH.sub.3                                                                            ##STR84##        1 0 117 (decomposes)                          ##STR85##     COOCH.sub.3       1 0 229 (decomposes)             "                                                                                          ##STR86##     "                 1 0 217 (decomposes)             "                                                                                          ##STR87##     "                 1 0 113 (decomposes)             "                                                                                          ##STR88##     "                 1 0  84 (decomposes)             "           .sup.++SO.sub.2C.sub.6 H.sub.5                                                               "                 1 0 139 (decomposes)             "                                                                                          ##STR89##                                                                                    ##STR90##        1 0 210 (decomposes)             "           COOCH.sub.2C.sub.6 H.sub.5                                                                   COOCH.sub.2C.sub.6 H.sub.5                                                                      1 0  70 (decomposes)             "           COOC.sub.6 H.sub.5                                                                           COOC.sub.6 H.sub.5                                                                              1 0 173 (decomposes)             "           COOC.sub.3 H.sub.7                                                                           COOC.sub.3 H.sub.7                                                                              1 0 150 (decomposes)              ##STR91##  .sup.++COOCH.sub.3                                                                            ##STR92##        1 0 oil                           ##STR93##                 COOCH.sub.3       1 0 221 (decomposes)              ##STR94##  "              "                 1 0 197 (decomposes)              ##STR95##  "              "                 1 0 221 (decomposes)              ##STR96##  "              "                 1 0  88 (decomposes)              ##STR97##  "              "                 1 0 180 (decomposes)              ##STR98##  "              "                 1 0 163 (decomposes)              ##STR99##  "              "                 1 0 158 (decomposes)              ##STR100## "              "                 1 0 206 (decomposes)              ##STR101## "              "                 0 0 250 (decomposes)              ##STR102## "              "                 1 0 181 (decomposes)              ##STR103## .sup.++COOCH.sub.3                                                                            ##STR104##       1 0 156 (decomposes)              ##STR105## COOCH.sub.3    COOCH.sub.3       0 1 120 (decomposes)              ##STR106## H              H                 1 0 94                           __________________________________________________________________________     .sup.++ isomer mixture; R.sup.2 and R.sup.3 are interchangeable          

EXAMPLE 3 ##STR107##

10 parts of the abovementioned Δ² -1,2,3-triazoline derivative and 3parts of trifluoroacetic acid are stirred for 5 hours in 50 parts ofmethylene chloride at room temperature. After the solvent has beendistilled off, the residue is digested with 30 parts of ether; yield: 8parts (88% of theory); m.p.: 195° C. (decomposes) (benzene/ligroin).##STR108##

4 parts of the abovementioned Δ² -1,2,3-triazoline derivative is heatedin 20 parts of dioxane for 6 hours at 100° C. After the solvent has beendistilled off, the residue is digested with 10 parts of petroleum ether;yield: 3 parts (85% of theory); m.p.: 159° C. (decomposes)(ether/petroleum ether).

The following compounds were prepared analogously:

    ______________________________________                                         ##STR109##                                                                                                 m.p.                                            R.sup.1       m       B       (°C.)                                    ______________________________________                                        H             0       --      115                                             C.sub.6 H.sub.5                                                                             0       --      149                                              ##STR110##   1                                                                                      ##STR111##                                                                            80                                              ##STR112##   0       --      140                                              ##STR113##   0       --      179 (decomposes)                                 ##STR114##   0       --      122 (decomposes)                                 ##STR115##   0       --      126 (decomposes)                                 ##STR116##   0       --      110 (decomposes)                                 ##STR117##   0       --      212 (decomposes)                                 ##STR118##   0       --       66                                              ##STR119##   0       --      169 (decomposes)                                 ##STR120##   0       --      194 (decomposes)                                 ##STR121##   0       --      203 (decomposes)                                 ##STR122##   0       --      146                                             ______________________________________                                    

EXAMPLE 4 ##STR123##

40 parts of the N-(p-bromophenyl)-Δ² -1,2,3-triazoline derivative isheated in 800 parts of xylene for 24 hours at 140° C. After the solventhas been distilled off, the residue is digested with 100 parts ofpetroleum ether; yield: 35 parts (92% of theory); m.p.: 170° C.(decomposes) (benzene/ligroin).

The following compounds were prepared analogously:

    ______________________________________                                         ##STR124##                                                                   R.sup.1     R.sup.2    R.sup.3    m.p. (°C.)                           ______________________________________                                        C.sub.6 H.sub.5CH.sub.2                                                                   COOCH.sub.3                                                                              COOCH.sub.3                                                                              140                                                                           (decomposes)                                C.sub.6 H.sub.5                                                                           "          "          187                                         "           COOC.sub.2 H.sub.5                                                                       COOC.sub.2 H.sub.5                                                                       109                                          ##STR125## COOCH.sub.3                                                                              COOCH.sub.3                                                                              168                                         "           COOC.sub.6 H.sub.5                                                                       COOC.sub.6 H.sub.5                                                                       117                                          ##STR126## COOCH.sub.3                                                                              "          174                                          ##STR127## "          "          209                                          ##STR128## "          "          153                                          ##STR129## COOCH.sub.3                                                                              COOCH.sub.3                                                                              197                                          ##STR130## "          "          175                                          ##STR131## "          "          178                                          ##STR132## "          "          190 (decomposes)                             ##STR133## "          "          258 (decomposes)                            ______________________________________                                    

EXAMPLE 5 ##STR134##

10 parts of the N-H-Δ² -1,2,3-triazoline derivative and 2 parts ofsodium methylate are stirred in 100 parts of tetrahydrofuran for 1 hourat room temperature. 8.6 parts of benzoyl chloride is then dripped inand the mixture stirred for a further two hours. After the precipitatehas been removed by suction filtration, the solvent is distilled off at50 mbars and the residue digested with 30 parts of ether; yield: 13parts (80% of theory); m.p.: 117° C. (decomposes). ##STR135##

3 parts of the N-H-aziridine derivative and 3 parts of triethylamine aredissolved in 50 parts of tetrahydrofuran. At 0° to 5° C. and whilestirring, 3.9 parts of benzene sulfochloride is dripped in. Afterremoval of the precipitated triethylammonium chloride by suctionfiltration, the solvent is distilled off. The residue is washed with 50parts of water and dried; yield: 5.4 parts (88% of theory); m.p.: 154°C. (decomposes).

The following compounds were prepared analogously:

    __________________________________________________________________________     ##STR136##                                                                   R.sup.1              n m B   m.p. .[°C.]                               __________________________________________________________________________    OCH.sub.3            1 1                                                                                ##STR137##                                                                       117 (decomposes)                                 OC.sub.3 H.sub.7     1 1                                                                                ##STR138##                                                                       118 (decomposes)                                  ##STR139##          1 1                                                                                ##STR140##                                                                       156 (decomposes)                                  ##STR141##          1 1                                                                                ##STR142##                                                                       169 (decomposes)                                  ##STR143##          0 1                                                                                ##STR144##                                                                       118 (decomposes)                                 N(CH.sub.3).sub.2    1 1                                                                                ##STR145##                                                                       108 (decomposes)                                 CH.sub.3             1 1                                                                                ##STR146##                                                                        79                                              HCCCH.sub.2          1 0 --   60                                               ##STR147##          1 0 --   66 (decomposes)                                  ##STR148##          1 0 --  159 (decomposes)                                  ##STR149##          1 1 S   164 (decomposes)                                  ##STR150##          1 1                                                                                ##STR151##                                                                       270 (decomposes)                                  ##STR152##          1 1                                                                                ##STR153##                                                                       155 (decomposes)                                 C.sub.6 H.sub.5NH    1 1                                                                                ##STR154##                                                                       163 (decomposes)                                 __________________________________________________________________________

EXAMPLE 6

Preparation of the starting compounds ##STR155##

At 65° C. and while stirring, a solution of 35 parts of KOH in 60 partsof methanol is dripped into 60 parts of compound III and 50 parts ofmethanol. The reaction mixture is then stirred for a further 2 hours at65° C. The solvent is subsequently distilled off at 50 mbars and theresidue is extracted several times with a total of 1,200 parts of ether.After distilling off the ether, there is obtained 38 parts of compoundVI (85% of theory; m.p. 94° C. from ligroin). ##STR156##

5 parts of compound VI, 7 parts of p-chlorobromoacetophenone and 3 partsof soda are stirred in 150 parts of ether for 24 hours at 34° C. Aftersuction filtration of the organic salts, the solvent and the residue aredigested with 50 parts of petroleum ether; 9.5 parts (91% of theory);m.p.: 111° C. (benzene/ligroin).

C. 17 parts of compound VI and 8.7 parts of methyl mustard oil areheated in 200 parts of benzene for 5 hours at 80° C. After the solventhas been distilled off, the residue is digested with 100 parts ofpetroleum ether; yield: 25 parts (97% of theory); m.p.: 116° C.(ethanol/ligroin). ##STR157##

At 80° C., 40.5 parts of azodicarboxylic acid diisopropyl ester isdripped into 20 parts of quadricyclane in 100 parts of benzene. Themixture is then heated for 24 hours at 80° C. and the solventsubsequently removed at 50 mbars; yield: 58 parts (98% of theory) of anoil.

The compounds in which R² and/or R³ denote H may also be present in theform of their salts, for instance as salts with mineral acids, e.g., ashydrochlorides.

The following compounds were prepared analogously:

    ______________________________________                                         ##STR158##                                                                   R.sup.2           R.sup.3     m.p. (° C.)                              ______________________________________                                                           ##STR159## 163 (decomposed)                                CH.sub.2COOCH.sub.3                                                                             COOCH.sub.3  76                                             SO.sub.2C.sub.6 H.sub.5                                                                         "           130                                              ##STR160##       "           128                                              ##STR161##       "           141                                              ##STR162##       "           164 (decomposed)                                 ##STR163##       "           128                                              ##STR164##       "           b.p. 100/1 mba                                   ##STR165##       "            73                                              ##STR166##       "            75                                              ##STR167##       "           oil                                              ##STR168##       "           135                                             C.sub.6 H.sub.5   C.sub.6 H.sub.5                                                                            98                                             C.sub.6 H.sub.5CH.sub.2                                                                         C.sub.6 H.sub.5CH.sub.2                                                                   oil                                             ______________________________________                                    

The compounds in Example 6 and the table were employed as startingcompounds for active ingredient syntheses (cf. tables relating toExamples 2 and 4).

The new active ingredients have a strong biological action on plants,i.e., they influence plant growth, either by reducing the growth height,by changing the concentration of the plant constituents, or bydestroying unwanted plants while not harming the crop plants.

Application may be effected for instance in the form of directlysprayable solutions, powders, suspensions, dispersions, emulsions, oildispersions, pastes, dusts, broadcasting agents, or granules byspraying, atomizing, dusting, broadcasting or watering. The forms ofapplication depend entirely on the purpose for which the agents arebeing used.

For the preparation of solutions, emulsions, pastes and oil dispersionsto be sprayed direct, mineral oil fractions of medium to high boilingpoint, such as kerosene or diesel oil, further coal-tar oils, etc. andoils of vegetable or animal origin, aliphatic, cyclic and aromatichydrocarbons such as benzene, toluene, xylene, paraffin,tetrahydronaphthalene, alkylated naphthalenes and their derivatives suchas methanol, ethanol, propanol, butanol, chloroform, carbontetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone,etc., and strongly polar solvents such as dimethylformamide, dimethylsulfoxide, N-methylpyrrolidone, water, etc. are suitable.

Aqueous formulations may be prepared from emulsion concentrates, pastes,oil dispersions or wettable powders by adding water. To prepareemulsions, pastes and oil dispersions the ingredients as such ordissolved in an oil or solvent may be homogenized in water by means ofwetting or dispersing agents, adherents or emulsifiers. Concentrateswhich are suitable for dilution with water may be prepared from activeingredient, wetting agent, adherent, emulsifying or dispersing agent andpossibly solvent or oil.

Examples of surfactants are: alkali metal, alkaline earth metal andammonium salts of ligninsulfonic acid, naphthalenesulfonic acid,phenolsulfonic acids, alkylaryl sulfonates, alkyl sulfates, and alkylsulfonates, alkali metal and alkaline earth metal salts ofdibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcoholsulfates, alkali metal and alkaline earth metal salts of fatty acids,salts of sulfated hexadecanols, heptadecanols, and octadecanols, saltsof sulfated fatty alcohol glycol ether, condensation products ofsulfonated naphthalene and naphthalene derivatives with formaldehyde,condensation products of naphthalene or naphthalenesulfonic acids withphenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylatedisooctylphenol, ethoxylated octylphenol and ethoxylated nonylphenol,alkylphenol polyglycol ethers, tributylphenol polyglycol ethers,alkylaryl polyester alcohols, isotridecyl alcohols, fatty alcoholethylene oxide condensates, ethoxylated castor oil, polyoxyethylenealkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycolether acetal, sorbitol esters, lignin, sulfite waste liquors and methylcellulose.

Powders, dusts and broadcasting agents may be prepared by mixing orgrinding the active ingredients with a solid carrier.

Granules, e.g., coated, impregnated or homogeneous granules, may beprepared by bonding the active ingredients to solid carriers. Examplesof solid carriers are mineral earths such as silicic acid, silica gels,silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bole, loess,clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate,magnesium oxide, ground plastics, fertilizers such as ammonium sulfate,ammonium phosphate, ammonium nitrate, and ureas, and vegetable productssuch as grain flours, bark meal, wood meal, and nutshell meal,cellulosic powders, etc.

The formulations contain from 0.1 to 95, and preferably 0.5 to 90, % byweight of active ingredient.

There may be added to the compositions or individual active ingredientsoils of various types, herbicides, fungicides, nematocides,insecticides, bactericides, trace elements, fertilizers, antifoams(e.g., silicones), and growth regulators.

Examples of herbicidally active compounds with which the activeingredients according to the invention may be combined are as follows:

    ______________________________________                                         ##STR169##                                                                   R                    R.sup.1                                                  ______________________________________                                         ##STR170##          NH.sub.2                                                  ##STR171##          NHCH.sub.3                                                ##STR172##          NHCH.sub.3                                                ##STR173##          NH.sub.2                                                  ##STR174##          NH.sub.2                                                 ______________________________________                                         ##STR175##                                                                   R              R.sup.1    R.sup.2                                             ______________________________________                                                        ##STR176##                                                                              H and salts                                         H                                                                                             ##STR177##                                                                              Cl and salts                                        H                                                                                             ##STR178##                                                                              F and salts                                         H                                                                                             ##STR179##                                                                              CH.sub.3 and salts                                  Cl.sub.2 OCH.sub.3                                                                            ##STR180##                                                                              H and salts                                          ##STR181##                                                                   ______________________________________                                         ##STR182##                                                                   R.sup.1        R.sup.2     R.sup.3                                            ______________________________________                                        CF.sub.3       nC.sub.3 H.sub.7                                                                          nC.sub.3 H.sub.7                                   CF.sub.3       nC.sub.3 H.sub.7                                                                          CH.sub.2CH.sub.2 Cl                                SO.sub.2 NH.sub.2                                                                            nC.sub.3 H.sub.7                                                                          nC.sub.3 H.sub.7                                   ______________________________________                                         ##STR183##                                                                   R.sup.1         R.sup.2 R.sup.3                                               ______________________________________                                        CH.sub.3        H                                                                                      ##STR184##                                            ##STR185##     H       i-C.sub.3 H.sub.7                                      ##STR186##     H                                                                                      ##STR187##                                            ##STR188##     H                                                                                      ##STR189##                                            ##STR190##     H       i-C.sub.3 H.sub.7                                      ##STR191##     H       CH.sub.2CCCH.sub.2 Cl                                  ##STR192##     H                                                                                      ##STR193##                                            ##STR194##     H       CH.sub.3                                               ##STR195##     H       CH.sub.3                                               ##STR196##                                                                   ______________________________________                                         ##STR197##                                                                   R.sup.1          R.sup.2     R.sup.3                                          ______________________________________                                         ##STR198##      H           C.sub.2 H.sub.5                                   ##STR199##      CH.sub.3    CH.sub.3                                          ##STR200##      H           CH.sub.3                                          ##STR201##      H           C.sub.2 H.sub.5                                   ##STR202##      H           CH.sub.3                                          ##STR203##      H           C.sub.2 H.sub.5                                  ______________________________________                                         ##STR204##                                                                   R.sup.1     R.sup.2     R.sup.3                                               ______________________________________                                        i-C.sub.3 H.sub.7                                                                         i-C.sub.3 H.sub.7                                                                         CH.sub.2CClCHCl                                       n-C.sub.3 H.sub.7                                                                         n-C.sub.3 H.sub.7                                                                         C.sub.2 H.sub.5                                       "           "           n-C.sub.3 H.sub.7                                     sec. C.sub.4 H.sub.9                                                                      sec. C.sub.4 H.sub.9                                                                      C.sub.2 H.sub.5                                       C.sub.2 H.sub.5                                                                           C.sub.2 H.sub.5                                                                            ##STR205##                                            ##STR206## C.sub.2 H.sub.5                                                                           C.sub.2 H.sub.5                                        ##STR207## C.sub.2 H.sub.5                                                                           C.sub.2 H.sub.5                                        ##STR208##                                                                   ______________________________________                                         ##STR209##                                                                   ______________________________________                                        C.sub.2 H.sub.5                                                               n-C.sub.3 H.sub.7                                                              ##STR210##                                                                   ______________________________________                                         ##STR211##                                                                   R.sup.1          X      Y       R.sup.2                                       ______________________________________                                        CH.sub.3         Cl     Cl      Na                                            Cl               Cl     Cl      Na                                            C.sub.2 H.sub.5  Cl     Cl      Na                                             ##STR212##      Cl     H       CH.sub.3                                       ##STR213##      H      H       H and salts                                    ##STR214##      H      Cl      NH.sub.4                                       ##STR215##      H      CH.sub.3                                                                              C.sub.2 H.sub.5                                ##STR216##      H      CH.sub.3                                                                              CH.sub.3                                        "              H      CH.sub.3                                                                              i-C.sub.3 H.sub.7                              ##STR217##      H      CH.sub.3                                                                               ##STR218##                                    ##STR219##      H      CH.sub.3                                                                              CH.sub.3                                       ##STR220##                                                                    ##STR221##                                                                   ______________________________________                                         ##STR222##                                                                   R.sup.1     X          R.sup.2                                                ______________________________________                                        i-C.sub.3 H.sub.7                                                                         Cl         C.sub.2 H.sub.5                                        "           Cl                                                                                        ##STR223##                                            "           Cl         i-C.sub.3 H.sub.7                                      C.sub.2 H.sub.5                                                                           Cl         C.sub.2 H.sub.5                                        "           Cl         C(CH.sub.3).sub.2 CN                                   "           Cl                                                                                        ##STR224##                                            "           Cl                                                                                        ##STR225##                                             ##STR226## Cl         (CH.sub.3).sub.2CH                                     "           Cl         tert. C.sub.4 H.sub.9                                  i-C.sub.3 H.sub.7                                                                         OCH.sub.3  i-C.sub.3 H.sub.7                                      "           SCH.sub.3  C.sub.2 H.sub.5                                        C.sub.2 H.sub.5                                                                           SCH.sub.3  C.sub.2 H.sub.5                                        "           SCH.sub.3  tert. C.sub.4 H.sub.9                                  ______________________________________                                         ##STR227##                                                                   X               Y           R                                                 ______________________________________                                        CF.sub.3        H           CH.sub.3                                          H               F           CH.sub.3                                          ______________________________________                                         ##STR228##                                                                   R.sup.1     R.sup.2        R.sup.3                                            ______________________________________                                         ##STR229##                                                                                ##STR230##    CH.sub.2 Cl                                         ##STR231##                                                                                ##STR232##    CH.sub.2 Cl                                         ##STR233## CH.sub.2CH.sub.2OCH.sub.3                                                                    CH.sub.2 Cl                                         ##STR234## CH.sub.2OCH.sub.3                                                                            CH.sub.2 Cl                                          "         CH.sub.2OCH.sub.3                                                                            CH.sub.2 Cl                                          "         CH.sub.2OC.sub.4 H.sub.9 n                                                                   CH.sub.2 Cl                                         ##STR235##                                                                                ##STR236##    CH.sub.2 Cl                                         ##STR237## H              --                                                  ##STR238## H                                                                                             ##STR239##                                          "         H              C.sub.2 H.sub.5                                     ##STR240## H              C(CH.sub.3).sub.2C.sub.3 H.sub.7                    ##STR241## H              CH.sub.3                                            ##STR242## H              CH.sub.3                                            ##STR243## H                                                                                             ##STR244##                                         ##STR245##                                                                   ______________________________________                                         ##STR246##                                                                   X           X.sup.1   R                                                       ______________________________________                                        Br          Br        H and salts                                             I           I         H and salts                                             Br          Br                                                                                       ##STR247##                                              ##STR248##                                                                   X = NO.sub.2                                                                  X = CN                                                                        ______________________________________                                         ##STR249##                                                                   R           R.sup.1   R.sup.2  R.sup.3                                        ______________________________________                                        Cl          Cl        Cl       H                                              F           Cl        Cl       H                                              Cl          Cl        H        H                                              Cl          CF.sub.3  H        COOH                                           Cl          Cl        H        COOCH.sub.3                                    NO.sub.2    CF.sub.3  H        H                                              H           CF.sub.3  Cl       H                                              H           CF.sub.3  Cl       OC.sub.2 H.sub.5                               Cl          Cl        H        OCH.sub.3                                      ______________________________________                                         ##STR250##                                                                   R.sup.1        R.sup.2  R.sup.3 R.sup.4                                       ______________________________________                                         ##STR251##    H        CH.sub.3                                                                              CH.sub.3                                       ##STR252##    H        CH.sub.3                                                                              CH.sub.3                                       ##STR253##    H        CH.sub.3                                                                              CH.sub.3                                       ##STR254##    H        CH.sub.3                                                                              CH.sub.3                                       ##STR255##    H        CH.sub.3                                                                              CH.sub.3                                       ##STR256##    H        CH.sub.3                                                                               ##STR257##                                    ##STR258##    H        CH.sub.3                                                                              CH.sub.3                                       ##STR259##    H        CH.sub.3                                                                              OCH.sub.3                                      ##STR260##    H        CH.sub.3                                                                              CH.sub.3                                       ##STR261##    H        CH.sub.3                                                                              OCH.sub.3                                      ##STR262##    H        CH.sub.3                                                                              CH.sub.3                                       ##STR263##    H        CH.sub.3                                                                              CH.sub.3                                       ##STR264##    H        CH.sub.3                                                                              OCH.sub.3                                      ##STR265##    H        CH.sub.3                                                                              CH.sub.3                                       ##STR266##    H        CH.sub.3                                                                              OCH.sub.3                                      ##STR267##    H        CH.sub.3                                                                              OCH.sub.3                                      ##STR268##    H        CH.sub.3                                                                              CH.sub.3                                       ##STR269##    CH.sub.3 H       CH.sub.3                                      ______________________________________                                         ##STR270##                                                                    ##STR271##                                                                    ##STR272##                                                                   ______________________________________                                         ##STR273##                                                                   R            R.sup.1          R.sup.2                                         ______________________________________                                        tert. C.sub.4 H.sub.9                                                                      NH.sub.2         SCH.sub.3                                       tert. C.sub.4 H.sub.9                                                                       ##STR274##      SCH.sub.3                                        ##STR275##  NH.sub.2         CH.sub.3                                        ______________________________________                                         ##STR276##                                                                   R.sup.1        R.sup.2    R.sup.3                                             ______________________________________                                        CH.sub.3       Br         sec. C.sub.4 H.sub.9                                CH.sub.3       Cl         tert. C.sub.4 H.sub.9                               CH.sub.3       Cl                                                                                        ##STR277##                                         CH.sub.2CH.sub.2CH.sub.2                                                                             ##STR278##                                             ______________________________________                                         ##STR279##                                                                          R.sup.1     R.sup.2                                                    ______________________________________                                               CH.sub.3    CH.sub.3                                                          CH.sub.3                                                                                   ##STR280##                                                 ##STR281##                                                                   ______________________________________                                         ##STR282##                                                                   R.sup.1     R.sup.2     R.sup.3                                               ______________________________________                                         ##STR283## sec. C.sub.4 H.sub.9                                                                      H                                                     "           tert. C.sub.4 H.sub.9                                                                     H                                                     "           "           CH.sub.3                                              H           CH.sub.3    H salts and esters                                    H           sec. C.sub.4 H.sub.9                                                                      H salts and esters                                    H           tert. C.sub.4 H.sub.9                                                                     H salts and esters                                    H           "           CH.sub.3 salts and esters                             ______________________________________                                         ##STR284##                                                                          R.sup.1                                                                ______________________________________                                                ##STR285##                                                                    ##STR286##                                                                    ##STR287##                                                             ##STR288##                                                                   ______________________________________                                         ##STR289##                                                                          R.sup.1     X                                                          ______________________________________                                               H           CH.sub.3 OSO.sub.3                                                Br          "                                                                 CH.sub.3    "                                                                 CH.sub.3    CF.sub.3 SO.sub.3                                           ##STR290##                                                                    ##STR291##                                                                    ##STR292##                                                                    ##STR293##                                                                    ##STR294##                                                                    ##STR295##                                                                    ##STR296##                                                                    ##STR297##                                                                    ##STR298##                                                                   ______________________________________                                         ##STR299##                                                                   R.sup.1     R.sup.2  R.sup.3  R.sup.4                                         ______________________________________                                        H           Cl       NH.sub.2 Cl                                              H           I        I        I                                               Cl          H        Cl       OCH.sub.3                                       Cl          Cl       H        Cl                                              Cl          Cl       Cl       OCH.sub.3                                       ______________________________________                                         ##STR300##                                                                   R.sup.1        R.sup.2  R.sup.3                                               ______________________________________                                         ##STR301##    H        H     salts, esters, amides                           "              CH.sub.3 H     "                                                ##STR302##    H        H     "                                               "              CH.sub.3 H     "                                                ##STR303##    H        H     "                                               "              CH.sub.3 H     "                                                ##STR304##                                                                    ##STR305##                                                                    ##STR306##                                                                    ##STR307##                                                                    ##STR308##                                                                    ##STR309##                                                                    ##STR310##                                                                    ##STR311##                                                                    ##STR312##                                                                    ##STR313##                                                                   ______________________________________                                         ##STR314##                                                                   R.sup.1                                                                       ______________________________________                                        OH                                                                            CH.sub.3                                                                       ##STR315##                                                                    ##STR316##                                                                    ##STR317##                                                                    ##STR318##                                                                    ##STR319##                                                                    ##STR320##                                                                    ##STR321##                                                                   ______________________________________                                         ##STR322##                                                                   R        R.sup.1  R.sup.2  R.sup.3 R.sup.4                                    ______________________________________                                        H        F.sub.3 C                                                                              H        C.sub.2 H.sub.5                                                                       C.sub.4 H.sub.9 n                          H        F.sub.3 C                                                                              H        nC.sub.3 H.sub.7                                                                       ##STR323##                                H.sub.3 C                                                                              H.sub.3 C                                                                              H        H                                                                                      ##STR324##                                H        F.sub.3 C                                                                              NH.sub.2 nC.sub.3 H.sub.7                                                                      nC.sub.3 H.sub.7                            ##STR325##                                                                    ##STR326##                                                                    ##STR327##                                                                    ##STR328##                                                                    ##STR329##                                                                    ##STR330##                                                                    ##STR331##                                                                    ##STR332##                                                                    ##STR333##                                                                    ##STR334##                                                                    ##STR335##                                                                    ##STR336##                                                                   ______________________________________                                         ##STR337##                                                                   R             R.sup.1         R.sup.2                                         ______________________________________                                        CH.sub.3      CH.sub.3        CH(C.sub.6 H.sub.3).sub.2                        ##STR338##   H               C.sub.2 H.sub.5                                  ##STR339##   iC.sub.3 H.sub.7                                                                              CH.sub.2 Cl                                      ##STR340##   CH.sub.2OC.sub.2 H.sub.5                                                                      CH.sub.2 Cl                                      ##STR341##   CH.sub.2CH.sub.2OCH.sub.3                                                                     CH.sub.2 Cl                                     CH.sub.2CHCH.sub.2                                                                          CH.sub.2CHCH.sub.2                                                                            CH.sub.2 Cl                                     ______________________________________                                    

In many instances it may be advantageous to combine or mix the compoundsaccording to the invention with other growth-regulating activeingredients, e.g., compounds of various chemical structure which formethylene (e.g., phosphonic acid derivatives and silanes, ethylhydrazines), and onium compounds (e.g., trimethylammonium, hydrazoniumand sulfonium salts, and derivatives of morpholinium, piperidinium andpyridazinium compounds). Also of interest are other growth-regulatingsubstances, for instance from the group oftrifluoromethylsulfonamido-p-acetotoluidides, maleic hydrazide, abscisicacid derivatives, chlorinated phenoxy fatty acids having an auxinicaction, and polyhydric alcohols and fatty acid esters having a specificaction on meristematic tissue areas.

The amount used of the agents according to the invention may vary, anddepends in the main on the type of effect desired.

The application rate is generally from 0.1 to 15 and more, preferablyfrom 0.2 to 6, kg of active ingredient per hectare.

The agents according to the invention influence the growth of plantparts above and in the soil in a different manner; employed in the usualconcentrations, they have a low toxicity to warm bloods.

The new agents have an effect on the physiology of plant growth and maybe used for various purposes. The different effects of these activeingredients depend in essence on the time of application, based on thedevelopment stage of the seed or plant, and on the concentrationsemployed.

The influence on vegetative development is manifested in particular in areduction in growth height, giving numerous plants, especially cereals,increased rigor and reducing the tendency toward lodging.Simultaneously, tillering is improved, resulting in an increase inear-bearing stems per unit area.

In grass, the reduced growth height gives a denser, more resistantsward, this in particular enabling the mowing frequency to be reduced.This is a considerable labor-saving advantage for lawns, grass vergesand in parks. The reduction in growth height is also accompanied by anincrease in the chlorophyll content, as a result of which grass andother plants take on a much deeper green.

The influence on vegetative growth also considerably increases floweringand fruiting in numerous plants, e.g., cotton and soybeans.

Of particular importance is the surprising phenomenon that treatmentwith the substances according to the invention induces rooting. Thisresults in a more rational use of water and nutrients by the treatedplants, thus increasing their resistance not only to dryness but also tocold (frost).

The possibilities of using the compounds of the invention in fruit andornamentals, in landscaping (including appropriate influence of thevegetation on barren land), and airfields and training grounds arevaried and extensive.

The substances may also be successfully used for hastening ripening andflowering, and in special methods of cultivation.

The new agents may also positively influence the concentration ofimportant plant constituents such as sugar and proteins.

The extent and degree of action depend on various factors, especiallythe time of application in relation to the development stage of theplant and the concentration employed. These factors are, in turn,different for different plant species and depend on the effect desired.For instance, lawns will be treated during the whole growth period;ornamentals in which it is desired to increase the bloom intensity andnumber of buds, before budding; and plants whose fruit is to used orprocessed, an appropriate length of time before the harvest. Variousderivatives of the class of compounds described here have herbicidalproperties, and are therefore suitable for removing and controllingunwanted plants.

EXAMPLES 7-10

Action on wheat, barley and oats

In the greenhouse, the four cereals wheat ("Opal" variety), rye("Petkuser"), barley ("Villa") and oats ("Flamingskrone") were sown inplastic dishes 11.5 cm in diameter in a sandy loam adequately suppliedwith nutrients. The active ingredients were applied at various rates tothe soil and to the leaves. When applied to the soil, the activeingredient were sprayed onto the surface of the soil on the day ofsowing; in the case of leaf treatment, the leaves were sprayed in theusual manner at a growth height of the plants of 10 cm. During the 18day growth period, the treated plants grew much more slowly than theuntreated control, a fact later confirmed by measurements of the stemlength. Measurements were taken of 100 plants from each series. As aresult of the use of transparent plastic dishes it was surprisinglyascertained that root growth had been promoted in the treated series.

The prior art agent used for comparison purposes wasN-2-chloroethyl-N,N,N-trimethylammonium cloride (CCC; German PrintedApplication DAS No. 1,294,734).

The results are given in the following tables.

EXAMPLE 7

    ______________________________________                                        Influence on the growth height                                                of wheat (soil and leaf treatment)                                                        Application                                                                   rate      Plant height                                            Active ingredient                                                                           kg/ha       in cm     relative                                  ______________________________________                                        (A) Soil treatment                                                            Control       --          31.0      100                                       CCC           0.5         26.0      83.9                                                    1.0         24.5      79.0                                                    2.0         22.5      72.6                                                    6.0         22.0      71.0                                       ##STR342##   0.5 1.0 2.0 6.0                                                                           28.5 23.0 20.5 10.5                                                                     91.9 74.2 66.1 33.9                        ##STR343##   0.5 1.0 2.0 6.0                                                                           27.5 22.5 15.5 11.5                                                                     88.7 72.6 50.0 31.7                       (B) Leaf treatment                                                            Control        --         30.0      100                                       CCC           0.125       28.0      93.3                                                    0.5         26.0      86.7                                                    1.0         26.0      86.7                                                    2.0         23.0      76.7                                                    4.0         23.0      76.7                                       ##STR344##   0.125 0.5 1.0 2.0 4.0                                                                     24.0 22.0 20.0 19.0 17.5                                                                80.0 73.3 66.6 63.3 58.3                   ##STR345##   0.125 0.5 1.0 2.0 4.0                                                                     25.0 23.5 21.0 21.5 20.0                                                                83.3 78.3 70.0 71.7 66.7                  ______________________________________                                    

EXAMPLE 8

    ______________________________________                                        Influence on the growth height of rye (soil and leaf treatment)                           Application                                                                   rate     Plant height                                             Active ingredient                                                                           kg/ha      in cm    relative                                    ______________________________________                                        (A) Soil treatment                                                            Control       --         29.0     100                                         CCC           0.5        28.0      96.6                                                     1.0        27.5      94.8                                                     2.0        28.0      96.6                                                     6.0        26.5      91.4                                        ##STR346##   0.5 1.0 2.0 6.0                                                                          22.5 19.0 13.0  8.5                                                                     77.6 65.5 44.8 29.3                         ##STR347##   0.5 1.0 2.0 6.0                                                                          23.0 22.5 19.0  9.0                                                                     79.3 77.6 65.5 31.0                        (B) Leaf treatment                                                            Control       --         29.5     100                                         CCC           0.125      29.0      98.3                                                     0.5        28.0      94.9                                                     1.0        27.5      93.2                                                     2.0        27.5      93.2                                                     4.0        29.0      98.3                                        ##STR348##   0.125 0.5 1.0 2.0 4.0                                                                    24.5 20.0 18.5 17.5 16.0                                                                83.1 67.8 62.7 59.3 54.2                    ##STR349##   0.125 0.5 1.0 2.0 4.0                                                                    25.0 20.5 22.0 18.0 18.5                                                                84.7 69.5 74.6 61.0 62.7                   ______________________________________                                    

EXAMPLE 9

    ______________________________________                                        Influence on the growth height of barley (soil and leaf treatment)                        Application                                                                   rate     Plant height                                             Active ingredient                                                                           kg/ha      in cm    relative                                    ______________________________________                                        (A) Soil treatment                                                            Control       --         31.5     100                                         CCC           0.5        28.0     88.9                                                      1.0        27.0     85.7                                                      2.0        26.0     82.5                                                      6.0        25.0     79.4                                         ##STR350##   0.5 1.0 2.0 6.0                                                                          28.0 28.0 23.5 16.5                                                                    88.9 88.9 74.6 52.4                          ##STR351##   0.5 1.0 2.0 6.0                                                                          30.5 29.0 24.5 19.0                                                                    96.8 92.1 77.8  60.3                        (B) Leaf treatment                                                            Control       --         30.0     100                                         CCC           0.125      29.0     96.7                                                      0.5        28.5     95.0                                                      1.0        26.5     88.3                                                      2.0        27.0     90.0                                                      4.0        27.0     90.0                                         ##STR352##   0.125 0.5 1.0 2.0 4.0                                                                    24.0 23.0 21.5 20.5 18.5                                                               80.0 76.7 71.7 68.3 61.7                     ##STR353##   0.125 0.5 1.0 2.0 4.0                                                                    25.5 23.5 22.0 20.5 20.0                                                               85.0 78.3 73.3 68.3 66.7                    ______________________________________                                    

example 10

    ______________________________________                                        Influence on the growth height of oats (soil and leaf treatment)                          Application                                                                   rate     Plant height                                             Active ingredient                                                                           kg/ha      in cm     relative                                   ______________________________________                                        (A) Soil treatment                                                            Control       --         28.0      100                                        CCC           0.5        28.0      100                                                      1.0        28.0      100                                                      2.0        27.0       96.4                                                    6.0        26.0       92.9                                       ##STR354##   0.5 1.0 2.0 6.0                                                                          25.0 24.0 21.0 15.0                                                                      89.3 85.7 75.0 53.6                        ##STR355##   0.5 1.0 2.0 6.0                                                                          28.0 26.5 24.5 15.5                                                                     100  94.6 87.5 55.4                         (B) Leaf treatment                                                           Control       --         28.0      100                                        CCC           0.125      28.0      100                                                      0.5        28.5      101.8                                                    1.0        28.0      100                                                      2.0        27.0       96.4                                                    4.0        25.5       91.1                                       ##STR356##   0.125 0.5 1.0 2.0 4.0                                                                    23.5 22.5 21.0 19.0 17.0                                                                 83.9 80.4 75.0 67.9 60.7                   ##STR357##   0.125 0.5 1.0 2.0 4.0                                                                    25.5 25.0 22.5 22.5 22.0                                                                 91.1 89.3 80.4 80.4 78.6                  ______________________________________                                    

EXAMPLE 11

Influence on stem length of cereals and Gramineae

The compounds listed in the following Tables A and B were examined bythe method described below as to their effect on the crop plants listedin these tables:

The vessels used for the experiments were plastic pots having a volumeof 1,130 cm³ (Table A) or paraffined paper cups having a volume of 170cm³ (Table B). The pots and cups were filled with a sandy loam. Theseeds of the test plants--separated by species--were sown shallow.Preemergence treatment (soil treatment) was effected immediately aftersowing and before germination of the seeds. Seeds lying on the surfacecame into contact with the active ingredients. Postemergence treatment(leaf treatment) took place at an average growth height of the plants(depending on the rate of growth) of from 6 to 10 cm. The substanceswere suspended, emulsified or dissolved in water as diluent and appliedby means of fine nozzles. The vessels were kept in the greenhouse in atemperature range of 12° C. to 25° C., and were regularly sprinklerirrigated for the duration of the experiment. The observation period was6 to 8 weeks.

Results

Tables (A) and (B) contain compounds which exercise a strong influenceon the development of the plant shoots. This growth inhibition of theparts of the plant above ground is desirable, and is not accompanied bydisadvantageous symptoms such as chlorosis. The treated plants wereusually conspicous for their dark green leaves.

EXAMPLE 11

                                      TABLE (A)                                   __________________________________________________________________________    Influence on the growth height of young cereal plants                                                Growth height in cm after                                                     soil treatment                                                                       leaf treatment                                                 Application rate                                                                      Triticum                                                                             Hordeum                                                                            Triticum                                   Active ingredient                                                                            kg/ha   aestivum                                                                             vulgare                                                                            aestivum                                   __________________________________________________________________________    Control        --      42     37   44                                          ##STR358##    0.5  1.0                                                                              40 40  36 31                                                                              40 40                                      CCC (prior art)                                                                              2.0     33     33   40                                          ##STR359##    0.5 1.0 2.0                                                                           16 15 0                                                                              40 39 38                                                                           42 27 20                                    ##STR360##    0.5 1.0 2.0                                                                           25 25 20                                                                             40 38 33                                                                           40 34 35                                    ##STR361##    0.5 1.0 2.0                                                                           40 40 30                                                                             48 44 41                                                                           40 39 40                                    ##STR362##    0.25  0.5 1.0 2.0                                                                     26 15 -- --                                                                          -- 43 40 30                                                                        29 25 13 12                                 ##STR363##    0.5 1.0 2.0                                                                           22 12 10                                                                             40 42 31                                                                           35 33 33                                    ##STR364##    0.5 1.0 24 20 16                                                                             38 30 27                                                                           33 28 17                                    ##STR365##    0.5 1.0 2.0                                                                           26 26 13                                                                             36 36 29                                                                           28 28 17                                    ##STR366##    0.25 0.5 1.0 2.0                                                                      32 28 20 23                                                                          --  36 39 31                                                                       30 23 26 20                                 ##STR367##    0.25 0.5 1.0 2.0                                                                      22 12 6 7                                                                            36 30 18 14                                                                        36 30 28 25                                __________________________________________________________________________

                                      TABLE (B)                                   __________________________________________________________________________    Influence on the growth height of Gramineae (soil and leaf treatment)                                 % growth inhibition compared with untreated                                   control after                                                                 soil treatment                                                                             leaf treatment                                           Application rate                                                                      Avena                                                                             Hordeum                                                                            Lolium                                                                            Avena                                                                             Hordeum                                                                            Lolium                          Active ingredient                                                                             kg/ha   sativa                                                                            vulgare                                                                            multifl.                                                                          sativa                                                                            vulgare                                                                            multifl.                        __________________________________________________________________________     ##STR368##     3.0     25  10    5  45  10   20                              CCC (bekannt)                                                                  ##STR369##     3.0     30  30   30  50  50   30                               ##STR370##     3.0     20   0    0  40  35   20                               ##STR371##     3.0     30  40    30.sup.+                                                                         40  30   25                               ##STR372##     3.0     60  35   --  20  20    0                               ##STR373##     3.0     60  60   50  60  50   50                               ##STR374##     3.0     40   60.sup.+                                                                          50  50  50   50                              __________________________________________________________________________      0 = no inhibition                                                            100 = no growth                                                               .sup.+ = leaf necroses due to too high phytotoxicity                     

EXAMPLE 12

Action on stem length, number of lateral shoots and yield in springbarley

To examine the effect of the various substances on spring barley up tothe maturity stage of the plants, an experiment was carried out in largepots. The plants were grown in quartz sand (fertilized with 2 g N asammonium nitrate in 3 doses, 1 g P₂ O₅ as secondary sodium phosphate,1.5 g K₂ O as potassium sulfate, 0.5 g MgO as magnesium sulfate, 10 mlof a solution of trace elements, and 10 mg of iron as an iron complex).The active ingredients were applid to the leaves twice, once at a rateof 0.5 kg/ha and once at a rate of 1.5 kg/ha, at a plant height of 35 to40 cm. The treated plants were up to 10% shorter than the control, andyields were also slightly up. The results of this experiment are givenbelow.

EXAMPLE 13

Action on grass or lawns

Lawn seed of the standard mixture Agrostis tenius (10%), Cynosuruscristatus (10%), Festuca rubra (15%), Lolium perenne (35%) and Poapraetensis (30%) was sown in a loam in large pots. The soil wasfertilized with 1.5 g N as ammonium nitrate and 1 g P₂ O₅ as secondarypotassium phosphate. After the grass had been cut twice, it was sprayedin conventional manner at a height of 4 cm with the active ingredientsat various application rates. 19 days after treatment the growth heightand dry substance content were determined. The treated grass was muchshorter than the control, and produced a correspondingly lower amount ofdry substance.

It was also observed that as the amount of compound according to theinvention increased the color of the grass turned an intensive deepgreen. The results of this experiment are given below. The prior artcompound used for comparison purposes was maleic hydrazide (M; GermanNo. 815,192).

EXAMPLE 12

    __________________________________________________________________________    Influence on stem length, number of lateral shoots and yield in spring        barley                                                                                          Stem length                                                                           No. of lateral shoots                                                                   Ear weight                                Active ingredient cm relative                                                                           no. relative                                                                            g   relative                              __________________________________________________________________________    Control           76.9                                                                             100  93  100   90.4                                                                              100                                   CCC          3 kg/ha                                                                            74.2                                                                             96.5 99  106.5 95.0                                                                              105.1                                  ##STR375##  0.5 kg/ha 1.5 kg/ha                                                                74.1 69.7                                                                        96.4 90.6                                                                          105 111                                                                           112.9 119.4                                                                         91.5 94.8                                                                         101.2 104.9                           __________________________________________________________________________

EXAMPLE 13

    __________________________________________________________________________    Action of grass or lawns                                                                                 19 days after                                                  Application                                                                         First cutting,                                                                         treatment              First cutting,                                                                chlorophyll                             rate  growth height                                                                          dry substance                                                                          Observations  content                     Active ingredient                                                                         kg/ha cm  relative                                                                           g   relative                                                                           (color)       g Ca + b/100 g              __________________________________________________________________________                                                      TS                          Control     --    25.5                                                                              100  12.5                                                                              100  normal green  1.33                        M           0.25  25.0                                                                              98.0 10.5                                                                              84.0 normal green  --                                      0.5   24.5                                                                              96.0 10.5                                                                              84.0 normal green  --                                      1.0   20.0                                                                              78.4  7.3                                                                              58.4 normal green  --                                      2.0   16.0                                                                              62.7  6.0                                                                              48.0 lighter green                                                                          reddish                                                                            1.11                                                                     brown in                                     4.0   12.5                                                                              49.0  4.5                                                                              36.0 lighter green                                                                          places                                                                             --                           ##STR376## 0.25 0.5 1.0 2.0 4.0                                                                26.0 24.0 19.0 16.0  10.5                                                         101.9  94.1  74.5  62.7  41.1                                                      10.7  8.6  7.0  4.8  3.1                                                          85.6 68.8 56.0 38.4 24.8                                                           normal green normal green normal                                              green dark green dark                                                                       -- -- -- -- --               ##STR377## 0.25 0.5 1.0 2.0 4.0                                                                25.0 24.0 21.5 18.0 12.5                                                          98.0 94.1 84.2 70.5 49.0                                                           12.8  11.4  8.4  6.3  4.1                                                         102.4  91.2  67.2  50.4  32.8                                                      normal green normal green normal                                              green dark green dark                                                                       -- -- -- 1.40 --            __________________________________________________________________________

EXAMPLE 14

Long-term action on lawns

A further experiment was carried out on lawns under the same conditionsas in Example 13. To investigate the long-term action of the compoundsof the invention, the growth of the grass was observed for 3 cuttingsafter treatment, and in the period of renewed growth after each cuttingthe shortening effect and the corresponding decrease in dry substancewere ascertained. The good long-term action of the agents examined isapparent from the following table. The prior art compound used forcomparison purposes was the diethanolamine salt of3-trifluoromethylsulfonamido-p-acetotoluidide (S; Proc. Northeast. WeedSci. Soc., 29, 403-408, 1975).

EXAMPLE 14

    __________________________________________________________________________    Long-term action on lawns                                                                        First cutting   Second cutting                                          Application      green           green                                                                              Third cutting              Active       rate  growth height                                                                            weight                                                                             growth height                                                                            weight                                                                             green weight               ingredient   kg/ha cm relative                                                                           g  relative                                                                           cm relative                                                                           g  relative                                                                           g  relative                __________________________________________________________________________    Control      --    18.0                                                                             100  35.3                                                                             100  14.7                                                                             100  26.7                                                                             100  15.2                                                                             100                     S            0.5   14.5                                                                             80.6 26.7                                                                             75.6 14.0                                                                             95.2 27.3                                                                             102.2                                                                              15.6                                                                             102.6                                1.0   13.0                                                                             72.2 23.0                                                                             65.2 12.5                                                                             85.0 27.6                                                                             103.4                                                                              15.0                                                                              98.6                                2.0   10.5                                                                             58.3 12.6                                                                             35.7  9.5                                                                             64.6 20.1                                                                              75.3                                                                              13.7                                                                              90.1                                4.0    9.0                                                                             50.0  9.4                                                                             26.6  4.5                                                                             30.6  9.6                                                                              36.0                                                                              10.4                                                                              68.4                    ##STR378##  0.5 1.0 2.0 4.0                                                                     14.5 12.5  11.0 10.5                                                             80.6 69.5 61.1 58.3                                                                25.5 24.4 22.0 16.5                                                              72.2 69.1 62.3 46.7                                                                14.5 11.5  8.0  7.0                                                              98.6 78.2 54.4 47.6                                                                27.8 25.1 18.7 13.2                                                              104.1  94.0  70.0  49.4                                                            16.5 16.5 14.0                                                                   108.6 108.6  92.1                                                             67.8                     ##STR379##  0.5 1.0 2.0 4.0                                                                     16.5 13.5 11.5  9.0                                                              91.7 75.0 63.9 50.0                                                                28.8 21.3 17.2 13.9                                                              81.6 60.3 48.7 39.4                                                                12.5  9.0  7.5  5.0                                                              85.0 61.2 51.0 34.0                                                                27.2 20.5 16.2 10.2                                                              101.9  76.8  60.7  38.2                                                            17.2 15.1 12.5                                                                   113.2   99.3  82.2                                                            4.5                      ##STR380##  0.5 1.0 2.0 4.0                                                                     18.5 16.5 14.5 12.5                                                              102.8  91.7  80.6  69.5                                                            31.8 27.1 20.3 19.5                                                              90.1 76.8 57.5 55.2                                                                14.0 13.0  9.0  7.0                                                              95.2 88.4 61.2 47.6                                                                28.8 25.8 19.1 16.8                                                              107.9  96.6  71.5  62.9                                                            15.5 15.3 12.8                                                                   102.0 100.7  84.2                                                             84.2                     ##STR381##  0.5 1.0 2.0 4.0                                                                     15.0 12.5  7.5   6.5                                                             83.3 69.5 41.7 36.1                                                                23.1 20.5  9.8  7.9                                                              65.4 58.1 27.8 22.4                                                                10.0  9.0 5.0 2.0                                                                68.0 61.2 34.0 13.6                                                                21.8 21.4 10.1  7.1                                                              81.6 80.1 37.8 26.6                                                                14.6 13.5  9.5                                                                   96.1 88.8 62.5                                                                52.0                     ##STR382##  0.5 1.0 2.0 4.0                                                                     14.0 14.0 12.5  9.5                                                              77.8 77.8 69.5 52.8                                                                26.8 25.5 20.0 13.2                                                              75.9 72.2 56.7 37.4                                                                13.0 12.5 22.0  7.5                                                              88.4 85.0 74.8 51.0                                                                23.5 22.0 21.4 15.3                                                              88.0 82.4 80.1 57.3                                                                16.5 16.3 15.7                                                                   108.6 107.2 103.3                                                             91.4                    __________________________________________________________________________

EXAMPLE 15

Action on individual grasses

Under the same conditions as in Example 13 the two grasses Festuca rubraand Poa praetensis (both components of the lawn mixture used in Example13) were grown in a neutral sandy loam. The growth height was measured 3weeks after treatment with the active ingredients. The results givenbelow demonstrate the shortening effect of the compounds of theinvention; Poa praetensis is influenced more strongly than Festucarubra.

EXAMPLE 15

    ______________________________________                                        Influence on the growth height of the grasses                                 Festuca rubra and Poa praetensis                                                          Appli-                                                                              Festuca rubra                                                           cation                                                                              growth height                                                                            Poa praetensis                                               rate     rela-   growth height                                    Active ingredient                                                                           kg/ha   cm     tive  cm   relative                              ______________________________________                                        Control       --      27.5   100   22.5 100                                   M             0.5     28.0   101.8 23.0 102.2                                               1.0     28.5   103.6 22.0 97.8                                                2.0     26.5   96.4  22.0 97.8                                   ##STR383##   0.5 1.0 2.0                                                                           27.0 25.5 23.5                                                                       98.2 92.7 85.5                                                                      20.0 20.0.sup.+  15.5.sup.+                                                        88.9 88.9 68.9                         ##STR384##   0.5  1.0 2.0                                                                          29.5 27.5 25.5                                                                       107.3 100.0  92.7                                                                   19.0 17.5.sup.+  14.0.sup.+                                                        84.4 77.8 62.2                        ______________________________________                                         .sup.+ plants a darker green                                             

EXAMPLE 16

Action of soybeans (hydroponic treatment)

Young soybean plants grown in quartz sand were transferred to hydroponictreatment in 4 liter vessels and provided with a sufficient supply ofnutrient solution and trace elements. The active ingredients were added(0.25 mg/vessel=0.06 ppm; 1.0 mg/vessel=0.25 ppm; 2.5 mg/vessel=0.63ppm) at a plant height of approx. 22 cm. The plants were in continuouscontact with the active ingredients. During the growth period of 4 weeksthe growth height of the treated plants was considerably reduced,compared with the control. The roots were also shorter, but the plantshad more and stronger shoots. The results are given below.

EXAMPLE 16

    __________________________________________________________________________    Influence on the growth of roots and shoots of soybeans (hydroponic           treatment)                                                                                Application                                                                         Shoot            Root                                                   rate  length  dry substance                                                                          length  dry substance                      Active ingredient                                                                         ppm   cm  rel.                                                                              g   rel. cm  rel.                                                                              g   rel.                           __________________________________________________________________________    Control      --   74.3                                                                              100 41.1                                                                              100  30.3                                                                              100 13.3                                                                              100                             ##STR385## 0.06 0.25 0.63                                                                      70.7 62.3 51.7                                                                    95.4 84.1 69.8                                                                    39.0 31.5 26.6                                                                    94.9 76.6 64.7                                                                     28.3 24.7 24.7                                                                    93.4 81.5 81.5                                                                    13.5 13.2 15.0                                                                     97.1  95.0 107.9              __________________________________________________________________________

EXAMPLE 17a-c

Action on soybeans, field beans and sunflowers

The action on soybeans, field beans and sunflowers was examined underthe same conditions as in Example 16. The shoots and roots of all 3 cropplants were considerably shortened. Whereas in the shoots the drysubstance was reduced commensurately with the shortening, the drysubstance in the roots rose (particularly in soybeans) as theconcentration increased. The results are given below.

EXAMPLE 17a

    __________________________________________________________________________    Action on soybeans(hydroponic treatment)                                                  Application                                                                         Shoot            Root                                                   rate  length  dry substance                                                                          length  dry substance                      Active ingredient                                                                         ppm   cm  rel.                                                                              g   rel. cm  rel.                                                                              g   rel.                           __________________________________________________________________________    Control      --   36.7                                                                              100 5.8 100  28.7                                                                              100 1.1 100                             ##STR386## 0.06 0.25 0.63                                                                      33.0 21.7 19.0                                                                    89.9 59.1 51.8                                                                    5.4 4.9 3.9                                                                       93.1 84.5 67.2                                                                     21.7 20.0 20.0                                                                    75.6 69.7 69.7                                                                    1.5 1.5 2.1                                                                       136.4 136.4 190.9              __________________________________________________________________________

EXAMPLE 17b

    __________________________________________________________________________    Action of field beans (hydroponic treatment)                                              Application                                                                         Shoot            Root                                                   rate  length  dry substance                                                                          length  dry substance                      Active ingredient                                                                         ppm   cm  rel.                                                                              g   rel. cm  rel.                                                                              g   rel.                           __________________________________________________________________________    Control      --   73.0                                                                              100 16.9                                                                              100  41.3                                                                              100 6.2 100                             ##STR387## 0.06 0.25 0.63                                                                      69.7 67.3 56.7                                                                    95.5 92.2 77.7                                                                    14.5 14.5 13.0                                                                    85.8 85.8 76.9                                                                     28.3 28.3 25.0                                                                    68.5 68.5 60.5                                                                    3.8 5.3 6.0                                                                       63.3 85.5 96.8                 __________________________________________________________________________

EXAMPLE 17c

    __________________________________________________________________________    Action on sunflowers (hydroponic treatment)                                               Application                                                                         Shoot            Root                                                   rate  length  dry substance                                                                          length  dry substance                      Active ingredient                                                                         ppm   cm  rel.                                                                              g   rel. cm  rel.                                                                              g   rel.                           __________________________________________________________________________    Control      --   41.3                                                                              100 6.4 100  20.0                                                                              100 1.5 100                             ##STR388## 0.06 0.25 0.63                                                                      35.0 27.3 27.3                                                                    84.7 66.1 66.1                                                                    6.3 5.3 5.2                                                                       98.4 82.8 81.3                                                                     18.7 16.7 12.7                                                                    93.5 83.5 63.5                                                                    1.5 1.4 1.6                                                                       100 93.3 106.7                 __________________________________________________________________________

EXAMPLE 18

Action on cotton

Cotton plants were subjected to hydroponic treatment under the sameconditions as in Example 16. The active ingredients were added (1.25mg/vessel=0.3 ppm and 5 mg/vessel=1.25 ppm) at a height of the plants of15 to 18 cm. During the 4 week growth period it was not only observedthat the treated plants were considerably shortened, but also that thebuds of the control plants and those treated with CCC withered in thenascent stage and dropped off, whereas the other treated plantsdeveloped a surprisingly large number of distinct squares. The resultsbelow are averages from 3 vessels, each of 3 plants.

EXAMPLE 18

    ______________________________________                                         Induction of flowering and influence on the growth height                    of cotton (hydroponic treatment)                                                                                 No. of                                                  Application           squares                                                 rate      Shoot length                                                                              per vessel                                 Active ingredient                                                                          ppm       cm      rel.  (3 plants)                               ______________________________________                                        Control      --        47.2    100   0                                        CCC          0.3       36.2    76.7  0                                                     1.25      34.8    73.8  0                                         ##STR389##  0.3 1.25  40.2 27.8                                                                             85.2 58.9                                                                           4.0 8.7                                   ##STR390##  0.3 1.25  41.9 30.9                                                                             88.8 65.5                                                                           2.6 8.3                                  ______________________________________                                    

EXAMPLE 19

Action on soybeans in a vegetation experiment in sandy soil

Soybean plants of the Gieso variety were grown in a neutral sandy loam.Fertilization took place at the time of sowing, with 0.5 g N as ammoniumnitrate and 1.0 g P₂ O₅ as secondary potassium phosphate. The activeingredients were applied to the soil at rates of 3 and 6 kg/ha at agrowth height of the plants of 10 to 12 cm.

After 4 weeks, the treated plants were much shorter than the control,and looked more compact as a result of the different angle of theleaves. The results are given below. The prior art compound used forcomparison purposes was 2,3,5-triiodobenzoic acid (T; U.S. Pat. No.2,978,838).

EXAMPLE 19

    ______________________________________                                        Action on soybeans in a vegetation experiment in a sandy loam                              Application rate                                                                        Growth height                                          Active ingredient                                                                            kg/ha       cm      relative                                   ______________________________________                                        Control        --          23.0    100                                        T              0.125       23.5    102.2                                                     0.375       25.0    108.7                                                     0.750       23.0    100.0                                       ##STR391##    3.0 6.0     15.0 14.0                                                                             65.2 60.9                                   ##STR392##    3.0 6.0     17.5 14.5                                                                             76.1 63.0                                   ##STR393##    3.0 6.0     13.5 12.5                                                                             58.7 54.4                                   ##STR394##    3.0 6.0     17.5 13.5                                                                             76.1 58.7                                   ##STR395##    3.0 6.0     14.0 14.0                                                                             60.9 60.9                                   ##STR396##    3.0 6.0     21.0 17.0                                                                             91.3 73.9                                   ##STR397##    3.0 6.0     17.0 16.0                                                                             73.9 69.6                                  ______________________________________                                    

EXAMPLE 20

Action on sugar beet

Sugar beets of the KAWpoly variety were grown in a neutral sandy loam inlarge pots. Fertilization with 1.5 g N as ammonium nitrate and 1 g P₂ O₅as secondary potassium phosphate took place at the time of sowing. At aplant height of 16 to 18 cm the leaves were treated twice, once with 0.5kg/ha and once with 1 kg/ha; in each case, 4 pots formed a variation ofthe experiment. After harvesting, the yield and sugar content in thebeets and the lower stems were found to have been improved by thetreatment. The results are given in the following table.

EXAMPLE 20

    __________________________________________________________________________    Influence on yield and sugar content of sugar beet                                                                  Sugar content of                                    Application                                                                         Yield      Sugar content                                                                          lower stems                                         rate  g dry sub- % in dry % in dry                                Active ingredient                                                                         kg/ha stance/vessel                                                                        rel.                                                                              substance                                                                          rel.                                                                              substance                                                                          rel.                               __________________________________________________________________________    Content     --    12.4   100 50.3 100 22.7 100                                 ##STR398## 0.5 1.0                                                                             13.04 14.39                                                                          107.4 118.5                                                                       51.0 52.2                                                                          101.4 103.8                                                                       22.9 25.8                                                                          100.9 113.6                        __________________________________________________________________________

EXAMPLE 21

Influence on the sugar content of sugar beet in the open

The active ingredient was applied to small plots in an ordinary beetfield to demonstrate the positive influence on sugar production underfield conditions. The crop plant was Beta vulgaris sap. altissima,variety "Kleinwanzleben KAWPoly". The soil was a sandy loam (1.5%organic substance, pH 5.7). Mineral fertilization totalled 400 kg N, 100kg P₂ O₅, and 100 kg K₂ O per hectare. For chemical weed control, 2.5kg/ha of 1-phenyl-4-amino-5-chloropyridazone-(6) was applied beforeemergence of the beet plants. Aphids were controlled with dimethoate(0,0-dimethyl-S-(N-methylcarbonylmethyl)-phosphorus dithioate). Sowingtook place on March 10, 1975. The beets were lifted comparatively earlyon September 29, 1975. The active ingredient was applied with the aid ofspraying equipment with fine nozzles, mounted on a tractor. The amountof water used for dispersion purposes was 780 liters/ha. Treatment waseffected on 2 different dates and on different plots:

I. the beet had 5 to 7 true leaves;

II. five weeks before harvesting, on the well developed plants.

The sugar content was determined from fresh beets immediately afterlifting.

The following results may be recorded:

(1) There was no impairment of the beets during the growth period.

(2) The sugar yields overall were low as a result of the early lifting.However, the sugar content was significantly improved by the activeingredient (cf. table).

The results with sugar beet are an indication of the increasedproduction of desirable plant constituents as a consequence of treatmentwith a representative of the class of compounds described.

EXAMPLE 21

    __________________________________________________________________________    Increase in the sugar content of sugar beet by chemical treatment in the      open                                                                                      Application                                                                   rate  Date                                                                              Sugar content in freshly lifted beet                    Active ingredient                                                                         kg/ha treated                                                                           absolute %                                                                           relative increase                                __________________________________________________________________________    Control      --    -- 12.6 a.sup.++                                                                        100                                               ##STR399## 2.0 2.0                                                                             I.sup.+  II                                                                       14.35 b 13.85 ab                                                                     113 110                                          __________________________________________________________________________     .sup.+ I = 20.05.75 Harvest: 29.09.75                                         II = 21.08.75                                                                 .sup.++ Values which have letters in common are not significantly             different (Duncan's new multiple range test, level 0.05%).               

EXAMPLE 22

Action on tomatoes

Tomatoes were grown in the greenhouse in glass dishes 11.5 cm indiameter containing a peat substrate which was provided with an adequatesupply of nutrients. The active ingredients were sprayed onto the leavesin conventional manner at a plant height of 9 to 12 cm. After 14 daysthe treated plants were shorter than the control, and had a deepercolor.

    ______________________________________                                                    Application rate                                                                         Plant height                                           Active ingredient                                                                           kg/ha        cm      relative                                   ______________________________________                                        Control        --          27.2    100                                         ##STR400##   1.5 3.0 6.0  24.3 20.3 14.0                                                                        89.3 74.6 51.5                              ##STR401##   1.5 3.0 6.0  25.0 22.7 15.3                                                                        91.9 83.5 56.2                             ______________________________________                                    

EXAMPLE 23

Action on rice

Rice was grown in the greenhouse under the same conditions as in Example22. At a growth height of 11 to 13 cm the active ingredients weresprayed onto the leaves in the usual manner. The plants were measuredafter 66 days. The treated plants were up to 30% shorter than thecontrol.

    ______________________________________                                                    Application rate                                                                         Plant height                                           Active ingredient                                                                           kg/ha         cm     relative                                   ______________________________________                                        Control        --          40.6    100                                        CCC           1.0          38.0    93.6                                                     2.0          40.5    99.8                                                     4.0          38.5    94.8                                                     6.0          40.0    98.5                                        ##STR402##   1.0 2.0 4.0 6.0                                                                            35.0 33.0 29.5 28.5                                                                   86.2 81.3 72.7 70.2                         ##STR403##   1.0 2.0 4.0 6.0                                                                            37.0 37.0 34.5 33.5                                                                   91.1 91.1 85.0 82.5                        ______________________________________                                    

EXAMPLE 24

Action on sunflowers

Sunflowers were grown under the same conditions as in Example 22. Theactive ingredients were applied both to the soil and to the leaves. Bothmethods of treatment resulted in much shorter plants than the control.

    ______________________________________                                                    Application rate                                                                         Plant height                                           Active ingredient                                                                            kg/ha        cm     relative                                   ______________________________________                                        (A) Soil treatment                                                            Control        --          36.3    100                                        CCC            3.0         40.0    110                                                      12.0         36.0     99                                         ##STR404##    3.0 12.0    26.5 15.5                                                                              73  43                                     ##STR405##    3.0 12.0    30.5 22.5                                                                              84  62                                    (B) Leaf treatment                                                            Control        --          38.3    100                                        CCC            1.5         38.0     99                                                       6.0         32.5     85                                         ##STR406##    1.5  6.0    30.0 25.5                                                                              78  67                                     ##STR407##    1.5  6.0    33.0 30.0                                                                              86  78                                    ______________________________________                                    

EXAMPLE 25

Herbicidal action

The new compounds listed in Tables 1 to 3 below have proved to beeffective in the control of unwanted plants. The following test methodwas employed.

Paraffined paper cups having a volume of 170 cm³ were filled with asandy loam, and the seeds of the test plants sown therein, separated byspecies. (The species are also listed below.)

In the first group, treatment was effected immediately after sowing andbefore germination of the seeds (preemergence treatment=soil treatment).Shallow sown seeds not completely covered with soil came into contactwith the active ingredients. In the second group, the plants weretreated postemergence (=leaf treatment) at a growth height of from 2 to8 cm, depending on the rate of growth and shape of the speciesconcerned. The compounds were suspended or emulsified in water andapplied with the aid of fine nozzles. The amounts applied are given inTables 1 to 3. The soil and plants were thoroughly sprinkler irrigatedfor the duration of the experiment. The cups were placed in thegreenhouse and kept in the temperature range 12°-25° C. or 18°-35° C.,depending on the temperature requirements of the various species. After2 to 6 weeks the action was assessed visually on a 0 to 100 scale, 0denoting no damage and 100 denoting plants not germinated or completelydestroyed.

List of plants employed in Tables 1 to 3:

    ______________________________________                                        Latin name         English name                                               ______________________________________                                        Alopecurus myosuroides                                                                           Blackgrass                                                 Cynodon dactylon   Bermudagrass                                               Cyperus esculentus Yellos nutsedge                                            Datura stramonium  Jimson weed                                                Digitaria sanguinalis                                                                            Hairy crabgrass                                            Echinochloa crus-galli                                                                           Barnyardgrass                                              Euphorbia spp.     Spurge family                                              usually E. geniculata                                                         Eleusine indica    Goosegrass                                                 Galium aparine     Catchweed bedstraw                                         Ipomoea spp.       Morningglory                                               usually I. lacunosa                                                           Matricaria chamomilla                                                                            Wild chamomile                                             Panicum virgatum   Switchgrass                                                Poa annua          Annual bluegrass                                           Setaria faberii    Giant foxtail                                              Sinapis alba       White mustard                                              Solanum nigrum     Black nightshade                                           Sorghum halepense  Johnsongrass                                               Stellaria media    Chickweed                                                  ______________________________________                                    

Results (Tables 1, 2, 3)

(1) The herbicidal action of the new compounds in combatting andcontrolling unwanted plant growth was confirmed. This action wasobserved on monocotyledonous and dicotyledonous species, and with pre-and postemergence application. Representatives of widely varyingbotanical families were investigated.

(2) Herbaceous crop plants were not very resistant to the compoundsgiven in Tables 1 to 3 (soil and leaf treatment). However, the compoundsare suitable for removing and suppressing unwanted plants when atechnique is employed in crop plants in which the active ingredients donot come into direct contact with the young leaves of the crop plants(postdirected spray, lay-by treatment, granulation of the activeingredients). It is also possible to apply the compounds to perennialspecies after cutting or during dormancy. A further field is weedcontrol in woody crop plants such as berry bushes and trees of allkinds. Unwanted plants can also be removed or suppressed in loci whereno account need be taken of crop plants.

                                      TABLE 1                                     __________________________________________________________________________    Herbicidal action - preemergence application                                  __________________________________________________________________________                     Appli-                                                                        cation                                                                            Test plants and % age damage                             Active           rate                                                                              Alopecurus                                                                           Cynodon                                                                            Cyperus                                                                             Digitaria                                                                           Euphorbia                                                                           Ipomoes                    ingredient       kg/ha                                                                             myosuroides                                                                          dactylon                                                                           esculentus                                                                          sanguinalis                                                                         spp.  spp.                       __________________________________________________________________________     ##STR408##      2.0 4.0                                                                           -- 85   70 90                                                                              27 55                                                                              100  --                                                                              -- --                                                                               50 60                      ##STR409##      2.0 4.0                                                                           70 83   65 90                                                                              45 60                                                                               70 100                                                                              90 100                                                                               -- 29                     ##STR410##      2.0 4.0                                                                           55 70   80 100                                                                             55 55                                                                               -- --                                                                               -- --                                                                                0 10                      ##STR411##      2.0 4.0                                                                           40 40   83 100                                                                             0 0  100 100                                                                              90 100                                                                              78 75                      ##STR412##      2.0 4.0                                                                           80 80   90 100                                                                             0 0    68 90                                                                              65 90                                                                               78 --                     __________________________________________________________________________                     Appli-                                                                        cation                                                                            Test plants and % age damage                             Active           rate                                                                              Matricaria                                                                          Panicum                                                                            Poa Setaria                                                                           Sinapis                                                                           Sorghum                                                                            Stellaria                    ingredient       kg/ha                                                                             chamomilla                                                                          virgatum                                                                           annua                                                                             faberii                                                                           alba                                                                              halepense                                                                          media                        __________________________________________________________________________     ##STR413##      2.0 4.0                                                                           95 -- 100  --                                                                             95 --                                                                             97 100                                                                            99 100                                                                            75 100                                                                            100  --                       ##STR414##      2.0 4.0                                                                           95 -- 100  --                                                                             57 --                                                                             59 65                                                                             74  74 78                                                                             100  --                       ##STR415##      2.0 4.0                                                                           -- --  -- --                                                                              -- --                                                                             80 90                                                                             80 95                                                                             90 90                                                                              -- --                        ##STR416##      2.0 4.0                                                                           -- --  -- --                                                                              65 --                                                                             55 100                                                                            98 --                                                                             55 55                                                                              -- --                        ##STR417##      2.0 4.0                                                                           -- --  -- --                                                                              70 --                                                                             40 100                                                                            90 --                                                                             53 50                                                                              -- --                       __________________________________________________________________________     0 = no damage                                                                 100 = complete destruction                                               

                                      TABLE 2                                     __________________________________________________________________________    Herbicidal action of a new compound and comparative agents - pre- and         postemergence                                                                 application                                                                                  Appli-                                                                        cation                                                                            Appli-                                                                            Test plants and % age damage                                          rate                                                                              cation                                                                            Alopecurus                                                                           Echinochloa                                                                          Galium                                                                            Sinapis                              Active ingredient                                                                            kg/ha                                                                             method                                                                            myosuroides                                                                          crus galli                                                                           aparine                                                                           alba                                 __________________________________________________________________________     ##STR418##    1.0 2.0                                                                           PRE PRE                                                                           0 0    80 90  -- --                                                                             90 90                                prior art (Belgian 668,018)                                                                  1.0 POST                                                                              70     100    --  100                                                 2.0 POST                                                                              70     100    --  100                                                 4.0 POST                                                                              --     --     50  --                                    ##STR419##    1.0 2.0                                                                           PRE 0 0E   80 90  -- --                                                                             60 60                                prior art (Farm Chemical                                                                     1.0 POST                                                                              80     100    --  100                                  Handbook 1975, Meister                                                                       2.0 POST                                                                              80     100    --  100                                  Publishing Co, USA, p. D50                                                                   4.0 POST                                                                              --     --     0   --                                    ##STR420##    1.0 2.0                                                                           PRE PRE                                                                           20 78  100 100                                                                              -- --                                                                             0 0                                  prior art (Chem. Week,                                                                       1.0 POST                                                                              40     98     --  0                                    26.7.1972, p. 21)                                                                            2.0 POST                                                                              50     98     --  0                                                   4.0 POST                                                                              --     --     0   --                                    ##STR421##    1.0 2.0                                                                           PRE PRE                                                                           80 95  85  85 -- --                                                                             100 100                                             1.0 POST                                                                              30     95     --  100                                                 2.0 POST                                                                              70     100    --  100                                                 4.0 POST                                                                              --     --     50  --                                   __________________________________________________________________________     0 = no damage                                                                 100 = complete destruction                                               

                                      TABLE 3                                     __________________________________________________________________________    Herbicidal action of new compounds and comparative agents -                   pre- and postemergence application                                            __________________________________________________________________________                      Application Test plants and % age damage                                      rate  Application                                                                         Alopecurus                                                                           Datura                                                                              Digitaria                                                                           Eleusine                     Active ingredient kg/ha method                                                                              myosuroides                                                                          stramonium                                                                          sanguinalis                                                                         indica                       __________________________________________________________________________     ##STR422##       2.0 4.0 8.0 2.0 4.0 8.0                                                             PRE PRE PRE POST POST POST                                                          95 95 98 25 25 30                                                                    -- -- -- 30 40 60                                                                   -- -- -- 80 80 90                                                                   -- -- -- 50 50 50             ##STR423##       2.0 4.0 8.0 2.0 4.0 8.0                                                             PRE PRE PRE POST POST POST                                                          30 25 25 15 22 38                                                                    -- -- -- 95 95 100                                                                  -- -- -- 50 70 90                                                                   -- -- -- 40 50 50             ##STR424##       2.0 4.0 8.0 2.0 4.0 8.0                                                             PRE PRE PRE POST POST POST                                                          68 85 98 28 38 35                                                                    -- -- -- 10 20 60                                                                   -- -- -- --  -- --                                                                  -- -- -- -- -- --            __________________________________________________________________________                      Application Test plants and % age damage                                      rate  Application                                                                         Galium  Lamium                                                                             Poa   Solanum                      Active ingredient kg/ha method                                                                              aparine                                                                              spp.  annua nigrum                       __________________________________________________________________________     ##STR425##       2.0 4.0 8.0 2.0 4.0 8.0                                                             PRE PRE PRE POST POST POST                                                          88 80 88 0 0 10                                                                      72 90 95 50 50 90                                                                   100 100 100 30 30 42                                                                85 85 90 22 22 38             ##STR426##       2.0 4.0 8.0 2.0 4.0 8.0                                                             PRE PRE PRE POST POST POST                                                          60 80 75 0 0 0                                                                       50 65 75 75 85 85                                                                   50 58 65 30 30 30                                                                   75 80 90 100 100 100          ##STR427##       2.0 4.0 8.0 2.0 4.0 8.0                                                             PRE PRE PRE POST POST POST                                                          70 80 90 5 5 5                                                                       25 60 85 0 10 20                                                                    95 98 100 35 35 40                                                                  0 15 25 10 10 20             __________________________________________________________________________                      Application Test plants and % age damage                                      rate  Application                                                                         Alopecurus                                                                           Datura                                                                              Digitaria                                                                           Eleusine                     Active ingredient kg/ha method                                                                              myosuroides                                                                          stramonium                                                                          sanguinalis                                                                         indica                       __________________________________________________________________________     ##STR428##       2.0 4.0 8.0 2.0 4.0 8.0                                                             PRE PRE PRE POST POST POST                                                          70 75 90 15 38 45                                                                    -- -- -- 60 95 100                                                                  -- -- -- 60 70 80                                                                   -- -- -- 90 90 90             ##STR429##       2.0 4.0 8.0 2.0 4.0 8.0                                                             PRE PRE PRE POST POST POST                                                          70 88 100 32 40 50                                                                   -- -- -- 50 60 65                                                                   -- -- -- 60 60 80                                                                   -- -- -- 60 60 70            __________________________________________________________________________                      Application Test plants and % age damage                                      rate  Application                                                                         Galium  Lamium                                                                             Poa   Solanum                      Active ingredient kg/ha method                                                                              aparine                                                                              spp.  annua nigrum                       __________________________________________________________________________     ##STR430##       2.0 4.0 8.0 2.0 4.0 8.0                                                             PRE PRE PRE POST POST  POST                                                         80 100 100 10 15 20                                                                  95 95 95 60 90 90                                                                   100 100 100 35 40 50                                                                95 95 95 85 100 100           ##STR431##       2.0 4.0 8.0 2.0 4.0 8.0                                                             PRE PRE PRE POST POST POST                                                          72 98 90 10 18 30                                                                    95 95 95 55 60 95                                                                   80 92 95 38 52 68                                                                   95 95 95 90 95 100           __________________________________________________________________________     0 = no damage                                                                 100 = complete destruction                                                    PRE = preemergence application                                                POST = postemergence application                                         

EXAMPLE 26

90 parts by weight of compound 1 is mixed with 10 parts by weight ofN-methyl-α-pyrrolidone. A mixture is obtained which is suitable forapplication in the form of very fine drops.

EXAMPLE 27

20 parts by weight of compound 2 is dissolved in a mixture consisting of80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to10 moles of ethylene oxide to 1 mole of oleic acid-N-monoethanolamide, 5parts by weight of the calcium salt of dodecylbenzenesulfonic acid, and5 parts by weight of the adduct of 40 moles of ethylene oxide to 1 moleof castor oil. By pouring the solution into 100,000 parts by weight ofwater and uniformly distributing it therein, an aqueous dispersion isobtained containing 0.02% by weight of the active ingredient.

EXAMPLE 28

20 parts by weight of compound 1 is dissolved in a mixture consisting of40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol,20 parts by weight of the adduct of 7 moles of ethylene oxide to 1 moleof isooctylphenol, and 10 parts by weight of the adduct of 40 moles ofethylene oxide to 1 mole of castor oil. By pouring the solution into100,000 parts by weight of water and uniformly distributing it therein,an aqueous dispersion is obtained containing 0.02% by weight of theactive ingredient.

EXAMPLE 29

20 parts by weight of compound 1 is dissolved in a mixture consisting of25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oilfraction having a boiling point between 210° and 280° C., and 10 partsby weight of the adduct of 40 moles of ethylene oxide to 1 mole ofcastor oil. By pouring the solution into 100,000 parts by weight ofwater and uniformly distributing it therein, an aqueous dispersion isobtained containing 0.02% by weight of the active ingredient.

EXAMPLE 30

20 parts by weight of compound 1 is well mixed with 3 parts by weight ofthe sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts byweight of the sodium salt of a ligninsulfonic acid obtained from asulfite waste liquor, and 60 parts by weight of powdered silica gel, andtriturated in a hammer mill. By uniformly distributing the mixture in20,000 parts by weight of water, a spray liquid is obtained containing0.1% by weight of the active ingredient.

EXAMPLE 31

3 parts by weight of compound 2 is intimately mixed with 97 parts byweight of particulate kaolin. A dust is obtained containing 3% by weightof the active ingredient.

EXAMPLE 32

30 parts by weight of compound 2 is intimately mixed with a mixtureconsisting of 92 parts by weight of powdered silica gel and 8 parts byweight of paraffin oil which has been sprayed onto the surface of thissilica gel. A formulation of the active ingredient is obtained havinggood adherence.

EXAMPLE 33

40 parts by weight of compound 1 is intimately mixed with 10 parts ofthe sodium salt of a phenolsulfonic acid-ureaformaldehyde condensate, 2parts of silica gel and 48 parts of water to give a stable aqueousdispersion. Dilution in 100,000 parts by weight of water gives anaqueous dispersion containing 0.04 wt% of active ingredient.

EXAMPLE 34

20 parts of compound 1 is intimately mixed with 2 parts of the calciumsalt of dodecylbenzenesulfonic acid, 8 parts of a fatty alcoholpolyglycol ether, 2 parts of the sodium salt of a phenolsulfonicacid-urea-formaldehyde condensate and 68 parts of a paraffinic mineraloil. A stable oily dispersion is obtained.

EXAMPLE 35

Further experiments were carried out in the greenhouse under theconditions described in Example 11. The plastic pots had a volume of 300cm³. As the plants which were examined liked the warmth (Euphorbiageniculata, Arachis hypogaea, Cynodon dactylon), they were kept at from20°-30° C. Cynodon dactylon from seed was cut once and the young growthtreated postemergence.

Results

Postemergence treatment with the compounds of the invention listed inTable 1 below resulted in a considerable (and desirable from the croppoint of view) reduction in shoot growth in groundnuts (Arachishypogaea) and Bermudagrass (Cynodon dactylon). The same effect can beachieved with a preemergence application, as shown for instance in Table2 at Euphorbia geniculata. It is particularly noteworthy that thecomparative agents only act on certain plant species. By contrast, thecompounds according to the invention act on a larger number of plantspecies. Similar effects were obtained with the new compounds insoybeans (Glycine max.), Indian corn (Zea mays) and other species.

                                      TABLE 1                                     __________________________________________________________________________    Growth-regulating action in groundnuts (A. hypogaea) and Bermudagrass         (C. dactylon) - postemergence application in greenhouse                                           Application                                                                         Test plants and growth height                                           rate  Arachis hypogaea                                                                        Cynodon dactylon                          Active ingredient   kg/ha cm   relative                                                                           cm   relative                             __________________________________________________________________________    Untreated control    --   16   100  11   100                                   ##STR432##         2.0 1.0 0.5                                                                          9 12 13                                                                           56 75 81                                                                           4 4 4                                                                              36 36 36                              ##STR433##         2.0 1.0 0.5 0.25                                                                    5 7.5 8 8                                                                          31 47 50 50                                                                        3 4 4 --                                                                           27 36 36 --                           ##STR434##         2.0 1.0 0.5                                                                         10 14 14                                                                           62 87 87                                                                           6 6 7                                                                              54 54 64                              ##STR435##         2.0 1.0 0.5                                                                         -- -- --                                                                           -- -- --                                                                           6 7 8                                                                              54 64 73                              ##STR436##         2.0 1.0 0.5 0.25                                                                    7 7 8 9                                                                            44 44 50 56                                                                         9 12 12  --                                                                        82 109  109  --                      ##STR437##         2.0 0.5                                                                             14 16                                                                               87 100                                                                            9 9  82 82                                prior art                                                                     __________________________________________________________________________

                  TABLE 2                                                         ______________________________________                                        Growth-regulating action in Euphorbia geniculata -                            preemergence treatment in greenhouse                                                          Appli-                                                                              Tests plants                                                            cation                                                                              and growth height                                                       rate  Euphorbia geniculata                                    Active ingredient kg/ha   cm        relative                                  ______________________________________                                        Untreated control --      11        100                                        ##STR438##       1.0 0.5 0.25                                                                          3 5 6     27 45 54                                  [ClCH.sub.2CH.sub.2N(C.sup.⊕H.sub.3).sub.3 ]Cl.sup.⊖                                1.0     9         82                                                          0.5     10        91                                        prior art         0.25    10        91                                         ##STR439##       1.0 0.5 0.25                                                                          10 12 12  91 109 109                                prior art                                                                     ______________________________________                                    

We claim:
 1. A polycyclic nitrogen-containing compound of the formula##STR440## where A denotes the radical --N═N--, B denotes the radicals--SO₂ --, ##STR441## --S--, C denotes the radicals --N═N-- or ##STR442##n denotes one of the integers 0 and 1, m denotes one of the integers 0and 1, and R¹ denotes 1,2-benzisothiazol-5-yl, and R² and R³ areidentical or different and each denotes (B)_(m) -R⁴, R⁴ having the samemeanings as R¹, and salts of these compounds.
 2. A process for reducingcrop plant growth height wherein the plants or the soil are treated withan effective amount of a polycyclic nitrogen-containing compound of theformula of claim 1 to reduce crop plant growth height.